Chloe Madison
  • Years in Tech


  • Current Role

    Product Designer, Undisclosed Company

  • Place of Origin

    Detroit, MI

  • Interview Date

    February 13, 2016

My past 4 years consisted of taking my background in broadcasting and love of technology and teaching myself motion graphics, web design, web development and then refining my interaction, UI, UX design skills before coming out to the Bay Area with little income and not finding a job for 4 months… in addition to going through a gender transition.

Why don’t we start from the beginning? Tell me a bit about your early years and where you come from.

I was born and raised in Michigan in the Metro-Detroit area. I was adopted and grew up actually quite privileged—my dad’s a lawyer. Growing up, I’ve never necessarily wanted or needed to want anything. But I definitely went through life questioning my gender which stemmed a lot of misguided anger that I have—at least I realize that now, looking back on those years.

I had a pretty normal childhood. I was definitely very nerdy and less masculine than the rest of the boys and got made fun of that and by the time high school came around, I figured, “Hey, smoking weed kind of helps me, you know, fit in with everybody else and forget about my gender issues. This fits.”  But by the end of freshman year, I was failing by a credit and my parents decided to send me to boarding school in Utah. I have a lot of feels about how they spent this ridiculous amount of money to force me back into not fitting in and living with these terrible boys who wanted nothing but to see the humor that was me losing my temper and attempting to fight them. All this instead of critically thinking about why I may be taking my issues out on drugs.

The drug use actually did get worse when I got back home and into my early to mid 20’s where I failed college. I ended up taking a couple years off though to regroup and ended up going to Broadcasting School which got me a job a few years later as a photojournalist in Northern Michigan, which is not where you want to be when you’re a queer person just starting to come to terms with your gender.

Where in Michigan? I love Michigan. I’ve almost moved to Detroit a couple of times.

I was in Cadillac, Traverse City, and Petoskey. That’s like—[puts hand up to represent the ‘mitten’ shape of Michigan] Here, here, here [points to areas near the fingertips on the left side]

I’ve been there!

Cabin fever set in after a little while and I didn’t really enjoy the work, and I wasn’t being paid well. At that point in time, I was ready to start talking to people who were questioning their gender so I could get a little bit better perspective, and those people weren’t available in northern Michigan. So I quit my job, and came back down to the Metro area, and started freelancing video productions and web design. Started getting really good with web design and after about a year of doing that, I realized I was actually doing the thing and making a living and I was really happy, but there was still something missing. That’s when I started my transition.

My transition actually went fairly well and mostly uneventful and I wonder why. My interactions with the shittiness of other people towards transwomen and transpeople in general, have come more recently rather than originally. It actually took until I went full-time to have my first truly awful experience. I’m well aware that I’ve been personally very privileged to have had a pretty uneventful transition, up until now.

So you went from photo journalism in northern Michigan to eventually product designer in San Francisco. How did that happen?

So, the thing about video production is that it take a lot from different visual and other mediums, graphic design being one that I excelled at.  Also, I had previous web development experience in high school. Actually, as early as middle school, I was taking my lunch break to work on my GeoCities site type of stuff, but moved away from it because web technologies associated with design were terrible up until about 2010.

I knew when I quit my job that video wasn’t going to pay the bills so I spent some time re-learning web technologies. I also had this theory that if most of my productions were going to end up online and I was building the content—why not also build the frame?  I started doing both concurrently and picked up new talents such as motion graphics (which translated really well to developing interaction prototypes) along the way though, after a while the video work kinda dried up and became a side gig. I just wasn’t very good at the hustle that was needed to procure video clients and convince them of the value of that work.

The web work eventually turned into more design focused work when a client of mine realized that was really where I shined. I was able to work on a few apps and some enterprise style websites that helped pad my portfolio.

So over the course of about a year I transitioned my work and life congruously, and at that point I was just bored of being freelance in Michigan, and kinda burnt out by the hours being high and the billable hours being low. I had always planned to come to the queer and tech mecca of SF, so I decided to put that together over about 7 months and flew here with a large suitcase, a backpack and a longboard that I had yet learned to ride.

What were your first impressions of Silicon Valley? What were you expecting? How did it live up, or not live up to your expectations?

It’s everything I hoped it to be, but I was definitely able to check my privilege quite a bit, moving out here, and see that it’s not all roses, and whatever that saying is. Life is lived out here, which is crazy. I was definitely sheltered from a lot of that, until I moved out here. A lot of my friends are struggling. In the past year I’ve made two friends who are homeless, and being able to help them where I can, and being able to see the struggle they deal with on the daily—it definitely allowed me to step back and think about how I see the world, and interact with people and create art.

When you moved to San Francisco, you were making 1,500 dollars a month, and it took you four months to find a full-time gig. Describe that time in your life.

So, I tried to find a roommate living situation before moving out here, but it didn’t work out, so I ended up paying for a month in an AirBnB hostel in the Outer Sunset where I lived with about 5-6 people while I looked for a more long-term living arrangement. After about 3 weeks I ended up finding a room in Oakland for $500 a month which was super lucky.

I actually ended up coming out here a week earlier than I planned because I had an interview with Charles Schwab fall in my lap. They ended up giving me some bullshit line of I’m too good for the job or something like that, you know, it was garbage. Apparently they changed the job description and are moving a lot of their jobs to Texas. I probably didn’t want to work there anyway.

Anyway, I got settled into Oakland and I was working on job hunting while fulfilling the hours I owed my client back in Michigan. I didn’t even get an interview for another 2 months. I think I really had to hone my resume to the Bay Area compared to what would have probably been acceptable in Michigan. I spent a lot of time working with the offerings at the SF LGBT center, specifically the TEEI program and the job clubs to update my resume. I had a lot of free time so I jumped on the opportunity to redesign my portfolio website as well as go to tech meet-ups and learn and connect with people. Also, of course, starting my life over and meeting new people, and learning to skateboard.

I ended up getting connected to my now boss randomly on Angel List—the only connection I had on there and he actually reached out to me before I even submitted to anyone. We had a couple of interviews. I wasn’t entirely sold on the job at first so I was a lot less on edge in the job interview and more myself, I guess you could say. You know, instead of the caricature of yourself you put on in job interviews. I think that helped. Anyways, I’ve been there since July in a contractor capacity and they’re officially hiring me next week.

Woo-hoo! Congrats!

Yeah. It was supposed to happen within three months, but we were also six months behind schedule on launching and everything, so… [chuckles]



I want to know more about Allytees.

Allytees? Did you go to the website?


So my best friend and I had been for a while thinking about different ways that we could give something to the LGBT community. The idea is that we have a way for allies of LGBT people to show their support by boldly claiming a person close to them is trans, gay, genderqueer, lesbian, asexual, etc. on a shirt. The shirt literally reads “my blank is a blank” or “My mom is a lesbian” or “My best friend is transgender.”

Now we could do this by having pages upon pages of items in an e-commerce site with all the different combinations of relationship to identification… but that would come out to something like 500 items for the variations of one product.  We could also have some dropdown to the side that the user could select, but that wasn’t any fun. We knew from the start that we had to allow the user to mockup the shirt on the shirt itself… something neither of us had ever seen before… here you’re given a product, an idea of a product, and here’s how you can modify it within these parameters. And I still have yet to see any website do that, where you actually mock up the product on the product itself.

It actually wouldn’t have been possible for us to do it if there weren’t the fulfillment options of direct to garment printing available. And at the time there was only one, and another one kind of getting its shit together. Now there’s like ten of them, literally like a year later, there’s like ten of these companies that allow you to send them orders over an API and they’ll print on demand and send to your customers. Joe and I actually needed some help with the API integration stuff and I was able to hire a developer—another trans woman—to do it.

It was nice to be able to invest in something for my community and also help get a solid portfolio piece on two people’s resume which eventually helped get us all jobs.

That’s really awesome.

Yeah, yeah, it was really nice.

What else has been really exciting to you about your work? What really activates you about design and product?

So what’s really gotten me is that this is real now. I’m a creative for a living which is freaky as hell, but I know this and much of the work is iterative and ultimately you end at those “aha” moment that really lift your spirits. It’s kind of a gut punch—a good gut punch—while you’re standing there looking at your work going  “Oh wait, fuck. Oh shit, that’s great!” Then you’re really excited about it. And then getting other people riled up about it as well and being a cheerleader for your own work is really the thing that moves me.

Improving on previous work is huge too. Knowing that you’re always learning. Maybe by the time you launch a design already feels long in the tooth, but you figure out what to do a couple weeks or months later and start working to implement the change.

Sometimes having to rush and put out work that you’re not entirely happy with but you end up getting positive feedback from is also kind of a stellar feeling. And being able to get to a point where I understand the logical aspect of why the design is the design. And why we have to push towards moving the design in this new direction because the current design is failing to keep up with the functionality. So it’s very much a whole brain task to do product design and that works with me very well. It’s very symbiotic with my personality and my ability as I generally approach product design, and other art I do in general, from both a creative and structural/logical perspective.

What been your experience been like in Silicon Valley as someone out as trans?

The thing is, I’ve never actually had the conversation, the trans conversation with my boss.


I know that I’m visibly trans, but I’ve never—that conversation has never come up.

That’s cool.

There were many times I would normally just talk about being trans, but I didn’t want to bring it up because I’ve been a contractor, and it’s easier to just say, “hey, goodbye contractor” than, “hey, goodbye employee.” But I’ve never had a problem with pronouns or anything like that. It weirds me out, but at the same time, I’m aware that I’m visible, so I’m not sure what’s going on in their heads at the same time so like whether, “Do they see it or do they not see it? Is it possible that they don’t see that I’m trans?” Who knows? I’m sure that conversation will come up at some point, especially once I start looking to use my benefits for my transition. I guess I’m just gonna ride this train as long as possible. Aside from being at work, I have felt, going to networking and stuff like that has been difficult. Never had any direct shittiness from people but kind of feel sometimes like I may not necessarily belong here.  So I definitely feel more comfortable in spaces of people who are marginalized. Like the “I Look Like An Engineer” campaign that went on. I was actually on the billboard, and was able to go to that, and that felt really good to be a part of stuff like that and I try to go to stuff like that and find a better community within the tech community with other people who aren’t cis white men. [chuckles]

Where do you find your support networks currently?

In my friends, actually mostly my partners. It’s actually nice now to have—back when I was freelancing, I didn’t really have much of a separation of work and play. And now I do, and in the past year, I’ve found that polyamory is kind of my M.O. for living my life with people that I care about. I find support in my partners, and the people who give a shit about me. I’ve found a lot of love in the Bay area since I’ve moved here, and it’s quite stunning. That’s really what keeps me going.

That’s beautiful. What is it like for you personally, straddling worlds of privilege like tech, and then other worlds that are underrepresented?

That’s a constant mental battle that I have. It’s something that I think about and unpack on a daily basis. I have these breakthroughs every once in awhile, where I’m like, ‘Okay. I don’t necessarily know how to express or talk about what I’m feeling with that.” But I want to make sure that I do right by my community and other communities that may need a collectively louder voice. It’s something that I’ve been more aware of since I moved out here and  I’ve been heavily unpacking it ever since.

I think mainly I want to use my art to help the community—you know—what I’m good at doing. I’ve been asked in the past to do things like canvassing and cold calling, which just makes me uncomfortable—makes all parties uncomfortable. I want to find ways where I can contribute in the highest capacity. For example the NTCE did a trans survey last year and needed a designer for the report. They were paying in this case, but I’d totally do something along those lines in my free time if an org needed it. I would have taken the NTCE, but I’m already slammed with two product launches coming up, so it was just bad timing.

I also have my own art projects that I can hopefully contribute to the zeitgeist that will push trans people forward.

Where do you see yourself in 5 or 10 years? Do you think you’ll still be here in the Valley?

I hope so. I really like Oakland. I really like my friends that I’ve made in the past year. I really like the opportunities that I have to create not only for myself, but also for all the cute queer trans kids. It’s quite magical here.

I’m looking forward to working on a few side projects. One is a slap-in-the-face video series about trans-women doing day to day things. I also have a longer mini-series that a friend is writing about a group of trans-women that I’ll be directing next year once pre-production is done. That’s a much a larger project.

Also working on a space for queer and trans artists to sell their wares. Kind of an extension of the Allytees thing, I think we did a lot right, but did a lot wrong, and I’ve been contemplating what the new brand will look like and how it will help to pay marginalized people for their ideas.

My last question for you would be, what advice would you give to folks from similar backgrounds to you who are hoping to get into tech or just make it work?

There are many factors and as I said before I’ve been very lucky to make it where I am today, but the core tenants of my being are having a passion for something and having some semblance of confidence in my ability to do the thing that I’m passionate about. But don’t be an asshole. If you come from a home that’s well off, it’s easy to dismiss things that you don’t understand or make fun of it, or assert your dominance over it. I mean, I could have very easily been a gatekeeper-type transwoman who tells other transwomen they’re not trans enough, but that’s never cool and shit like that needs to be called out. So, Wheaton’s law. Don’t be a dick.